Asymmetric reactions represent one of the most important developments of modern organic chemistry.1 Asymmetric reactions enable the synthesis of optically active compounds, which are highly desirable in the field of organic chemistry, and particularly in the pharmaceutical industry. Indeed, many drugs are required to be produced as single enantiomers (e.g. high optical purity), since it is often observed that only one of the enantiomers possesses the desirable drug profile. With the growing demand for effective and potent drugs, the development of novel asymmetric reactions has become paramount for the production of enantiomerically pure compounds.
Catalytic asymmetric reactions take advantage of chiral catalysts to produce enantiomerically pure or enriched compounds. The catalyst's chirality can originate from coordination to a chiral ligand. Examples of chiral ligands include BINAP,2 QUINAP,3 and BINOL4 (Scheme 1). These ligands can provide excellent enantioselectivity for various reactions, and have proven to be particularly effective in catalyzing asymmetric reactions when coordinated to transition metals.
A new class of chiral ligands for catalytic asymmetric reactions and other applications, including 1-(1,2,3,4-tetrahydroisoquinolin-1-yl)-naphthalen-2-ol (THIQNOL, Scheme 1), was disclosed by Li et al. in PCT/CA2007/000348, published under WO 2007/098608 A1.5,6

The present invention refers to a number of documents, the content of which is herein incorporated by reference in their entirety.